Increasing demands to be seen as authentic at work have created a paradox of self-presentation for employees: the desire to be seen as simultaneously true to self and professionally appropriate in workplace interactions. The present paper introduces one way in which individuals may navigate this tension: strategic authenticity, a self-presentational approach that involves enacting behaviors intended to increase colleagues’ perceptions of one’s authenticity while accounting for individual and contextual factors that influence one’s professional image. I propose that the behavioral signals of social deviations (nonconformity and spontaneity) and self-expressions (transparency and vulnerability) increase colleagues’ perceptions of a worker’s authenticity but pose a threat to their professional image. Next, I highlight how felt authenticity and the degree of perceived violation of social expectations (i.e., benign versus taboo signal content and aligning with communal versus agentic norms) moderate the impact of signals on perceptions of authenticity and professional image, suggesting that strategic authenticity can be achieved via a careful selection of behaviors based on individual and contextual factors. Last, I consider how the enactment of strategic authenticity leads to high-quality connections at work, which over time, may lead to the formation of positive relationships (enhanced by an actor’s felt authenticity). This paper extends prior scholarship on authenticity, professional image construction, and high-quality connections by highlighting how to balance interpersonal goals to appear authentic and at the same time, maintain a desirable professional image in workplace interactions.